22876-17-1

Basic information

• Product Name: 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE
• Synonyms: 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE;6-AMINO-2-(3H) BENZOXAZOLONE;2(3H)-BENZOXAZOLONE, 6-AMINO-;TIMTEC-BB SBB010320;2(3H)-Benzoxazolone,6-amino-(9CI);6-amino-1,3-benzoxazol-2(3H)-one(SALTDATA: FREE);6-Amino-2,3-dihydro-2-oxo-1,3-benzoxazole;6-aMinobenzo[d]oxazol-2(3H)-one
• CAS NO: 22876-17-1
• Molecular Formula: C₇H₆N₂O₂
• Molecular Weight: 150.13
• Product Categories: AMINEPRIMARY
• Mol File: 22876-17-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 205°C(lit.)
• Appearance: /
• Density: 1.438±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• PKA: 9.03±0.70(Predicted)
• CAS DataBase Reference: 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE(22876-17-1)
• EPA Substance Registry System: 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE(22876-17-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 22876-17-1(Hazardous Substances Data)

Usage

General Description

6-Amino-1,3-benzoxazol-2(3H)-one, also known informally as 1,3-Benzoxazol-2(3H)-one, 6-amino- is an organic compound and hypothesized intermediate in the synthesis of microbial secondary metabolites. 6-AMINO-1,3-BENZOXAZOL-2(3H)-ONE belongs to the family of benzoxazolones, which are heterocyclic compounds containing a benzene ring fused to an oxazolone ring, with its molecular formula written as C7H6N2O2. Its primary use remains largely restricted to scientific research, particularly within the context of chemical and biochemical reactions, due to its ability to react under various conditions. It is generally characterized by its reactivity and the specificity of its reactions.

InChI:InChI=1/C7H6N2O2/c8-4-1-2-5-6(3-4)11-7(10)9-5/h1-3H,8H2,(H,9,10)

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 121-88-0 5-Nitro-2-aminophenol 
• 38880-75-0 (2-hydroxy-4-nitro-phenyl)-carbamic acid ethyl ester 
• 4694-91-1 6-nitro-3H-benzooxazol-2-one 

Downstream Products

• 103391-39-5 diphenyl-acetic acid-(3-diphenylacetyl-2-oxo-2,3-dihydro-benzoxazol-6-ylamide) 
• 81110-79-4 (2-oxo-2,3-dihydro-benzoxazol-6-yl)-urea 
• 102024-56-6 N'-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-N,N-diphenyl-urea 
• 99584-10-8 6-amino-3-methyl-1,3-benzoxazol-2(3H)-one 
• 6885-65-0 [4-(2-oxo-2,3-dihydro-benzooxazol-6-ylsulfamoyl)-phenyl]-carbamic acid methyl ester 
• 948021-91-8 (R)-2-(4-(4-chloro-3-fluorophenyl)-3-methylpiperazin-1-yl)-2-oxo-N-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)acetamide 
• 948022-46-6 (R)-2-(4-(4-chloro-3-fluorophenyl)-2-methylpiperazin-1-yl)-2-oxo-N-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)acetamide 
• 948021-63-4 C₂₀H₁₈F₂N₄O₄ 
• 948021-64-5 C₂₀H₁₈F₂N₄O₄ 
• 948021-65-6 C₂₀H₁₉ClN₄O₄ 
• 948021-66-7 (R)-2-(4-(4-chlorophenyl)-3-methylpiperazin-1-yl)-2-oxo-N-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)acetamide 
• 948021-68-9 C₂₀H₁₉ClN₄O₄ 
• 948021-67-8 (R)-2-(4-(4-chlorophenyl)-2-methylpiperazin-1-yl)-2-oxo-N-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)acetamide 
• 948022-16-0 C₂₀H₁₉FN₄O₅ 

Relevant articles and documents

NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

Replacement of the Benzylpiperidine Moiety with Fluorinated Phenylalkyl Side Chains for the Development of GluN2B Receptor Ligands

The 4-benzylpiperidine moiety is a central structural element of potent N-methyl-d-aspartate (NMDA) receptor antagonists containing the GluN2B subunit. To obtain novel GluN2B ligands suitable for positron emission tomography, the benzylpiperidine moiety was replaced with fluorinated ω-phenylalkylamino groups. For this purpose three primary propyl- and butylamines 7 a–c and one butyraldehyde 7 d bearing a fluorine atom and an ω-phenyl moiety were prepared in 3- to 7-step syntheses. Compounds 7 a–d were attached to various scaffolds of potent GluN2B antagonists (scaffold hopping) instead of the original 4-benzylpiperidine moiety. Although benzoxazol-2-ones and indoles with a benzylpiperidine moiety show high GluN2B affinity, the corresponding fluorophenylalkylamine derivatives did not result in high Glu2B affinity. Moderate GluN2B affinity was observed for a 3-(fluoroalkyl)-substituted tetrahydro-1H-3-benzazepine (Ki=239 nm). However, high GluN2B affinity was obtained for the tetrahydro-5H-benzo[7]annulen-7-amines 12 a–c (Ki=17–30 nm). Docking studies resulted in the same binding pose for 12 a as for the lead compound Ro 25-6981. It can be concluded that some GluN2B ligands (benzoxazolones, indoles) do not tolerate replacement of the 4-benzylpiperidine moiety with flexible fluorinated phenylalkyl side chains, but other scaffolds such as tetrahydro-3-benzazepines and -benzo[7]annulenes retain interaction with NMDA receptors containing the GluN2B subunit.

Comparative study of conventional and microwave-assisted synthesis of novel 6-(arylideneamino)benzo[d]oxazol-2(3H)-ones with potential antibacterial activity

(Formula presented) The synthesis and characterization of novel class of Schiff bases derivatives 6-(Benzylideneamino)benzo[d]oxazol-2(3H)-ones (5a-d and 6a-d), derived from the condensation reactions of different aromatic aldehydes with 6-amino-2(3H)-benzoxazolone and 3-methyl-6-amino-2(3H)-benzoxazolone, using conventional and microwave irradiation methods was described. The structure of all newly synthesized compounds has been proven by using various spectral methods such as IR, 1H-NMR and 13C-NMR. The results confirmed that benzoxazolinonic amino group reacted with aromatic aldehydes to form the desired Schiff bases.